Dichloromethane → HCID 22182461, compound

HRID 1796810Notes

Reaction equation

HRID 1796810 reaction equation
ClCCl.[CH3:4][NH:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=3[CH3:32])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:10]([C:33]23OCC(C)(C[O:38]2)C[O:34]3)[CH:9]1[CH3:42])=[O:7].FC(F)(F)C(O)=O>O>[F:31][C:29]1[CH:28]=[CH:27][C:26]([CH3:32])=[C:25]([CH:30]=1)[CH2:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([S:14]([N:11]2[CH2:12][CH2:13][N:8]([C:6](=[O:7])[NH:5][CH3:4])[CH:9]([CH3:42])[CH:10]2[C:33]([OH:38])=[O:34])(=[O:16])=[O:15])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 69597599HCID 69597599, compound

Product 1

HCID 22182461HCID 22182461, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a dichloromethane (7 ml) solution of 4-[4-(5-fluoro-2-methyl-benzyloxy)-benzenesulfonyl]-2-methyl-3-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-piperazine-1-carboxylic acid methylamide (compound of formula XLIV, 376 mg, 0.67 mmol) at about 23° C. was added water (0.14 ml) and trifluoroacetic acid (0.14 ml). The reaction mixture was stirred for about 0.5 hour then was concentrated in vacuo. The residue was diluted with methanol (20 ml) and water (6 ml) and cesium carbonate (45 ml of a 10% solution in water) was added to the mixture. The reaction mixture was heated to about 40° C. for about 24 hours then was cooled to about 23° C., acidified with hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine and dried with sodium sulfate and concentrated in vacuo, to give 330 mg of a compound of formula XLVI.

Workup

  1. concentrationthen was concentrated in vacuo
  2. additionThe residue was diluted with methanol (20 ml) and water (6 ml) and cesium carbonate (45 ml of a 10% solution in water)
  3. additionwas added to the mixture
  4. temperaturethen was cooled to about 23° C.
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried with sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c33980ed2ba74a3cafe5ed8fb8bef2eb
Source dataset
uspto-grants-2006_04
Patent number
US07030242B2

Reaction notes

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